


Adventurous Babysitting

by Anonymess (Tecton)



Series: Life With Cole [1]
Category: The Babysitter (2017)
Genre: Consensual Underage Sex, F/F, F/M, Futanari, Futanari Sonya (The Babysitter), Multi, Open Relationships, Other, The Babysitter (2017) - Canon Divergence, The Babysitter (2017) Spoilers, Underage Kissing, Underage Oral Sex, Underage Relationship
Language: English
Status: In-Progress
Published: 2020-09-20
Updated: 2020-11-13
Packaged: 2021-03-08 01:35:38
Rating: Explicit
Warnings: Underage
Chapters: 3
Words: 4,278
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26557480
Author URL: https://archiveofourown.org/users/Tecton/pseuds/Anonymess
Summary: Take a pre-teen with an active imagination, a night of horror movies and a friend staying over.  Mix well, seasoning with a babysitter and her friends.
Relationships: Allison/Melanie/Sonya, Cole/Allison, Cole/Bee, Cole/Melanie, Cole/Melanie/Allison, Cole/Melanie/Bee, Cole/Sonya, Melanie/Bee, Melanie/Sonya, Sonya/Bee/Melanie, Sonya/Melanie/Cole
Series: Life With Cole [1]
Series URL: https://archiveofourown.org/series/1931413
Comments: 20
Kudos: 25





	1. Awake

**Author's Note:**

> So, this is a lot milder than my usual stuff. Just felt right. Also, for people who know the movie, you'll know where this splits off.

At first, Cole thought having a babysitter would be humiliating. No 12 year old wants people to know they have one. That their parents don't trust them alone. But, his parents were right to worry. Since he was small, Cole always had anxiety problems, and being home alone exacerbated them. So, they hired a sitter. Kind of a loose term, really. She was more like a friend. Bee. A beautiful blonde that Cole was somewhat smitten with. She would often come by when his parents were home, just to hang out. He met her friends because of this, and they all developed a fondness for the boy. Smarter and quicker-witted than other boys his age, he had a natural, awkward charisma. That was what drew his only same-aged friend, Melanie, to him.

Bee had four friends she hung around with: Max, the kind-hearted jock; John, the clown; Allison, the well-meaning airhead; and Sonya, the quiet, observant goth. Each, in their own way, helped Cole. Max taught him to stand up for himself and be more confident. This paid off with him knocking out local bully Jeremy. John taught him to relax and be more social. Allison helped with his wardrobe, since he dressed in old-fashioned clothes like a 1950's librarian stereotype. And Sonya, she helped him become better at talking to girls. Everything was rolling smoothly for the boy, going as well as anyone could hope for in their life.

Melanie lived across the street from him, and the two were unofficially boyfriend and girlfriend. It was odd for her, given that she had no interest in boys other than Cole, preferring girls. She was allowed to stay over sometimes, sleeping in one of three guest rooms in Cole's large house. Usually the one beside Cole's room. This was only allowed when his parents were out of town because Bee was ever present.

On this night, Cole had been watching a horror movie marathon all day with Melanie and Bee. Allison and Sonya were due over around the pre-teens' bedtime. Max and John had originally intended to come over, but had opted to take their girlfriends out for the evening instead, That would leave Cole as the only male in the house. After the marathon, Cole and Melanie are sent up to bed, the boy climbing into bed and cuddling up under the blanket. "Night, big guy." Bee whispers, kissing his forehead before leaving the room. He could hear the downstairs door open, Sonya and Allison's voices fading out as he drifts off to sleep.

Four hours later, he wakes with a start, covered in sweat. His heart was pounding so loudly he was sure the whole house could hear. A nightmare lingered at the edges of his mind. A book, a cult...and Bee trying to kill him, alongside her friends. _Never watching 'Sometimes They Come Back' before bed ever again..._ He grumbles internally, then slides out of bed. Opening his door, he hears soft snoring, peering over the railing to see Allison on the couch, curled under a blanket. Definitely her snoring. Making his way towards the stairs, he slows when he hears odd noises coming from Melanie's room. Creeping over and easing the door open a bit (while silently thanking his father for being so obsessive about not having squeaky doors), he sees something that freezes him in place.

Melanie was laying on the bed completely naked, Bee's fingers buried inside her. The sitter kissed along her neck and up to her lips, fingers digging in deeper. Transfixed by the sight, he holds his breath, afraid to make a single sound. That was when he noticed Sonya sitting in a chair in the corner, his eyes widening further. _Holy shit, Sonya has a dick!_ Not something he'd ever expected to discover about one of Bee's friends. When his gaze returns to Bee and Melanie, they're sitting up on the bed, looking towards him. "Might as well join us, Cole." Words he'd never expected to hear from Melanie...but probably the most welcomed sound he would hear in his life.

He slowly steps in, shutting the door behind him. Bee walks over, gently guiding him back to the bed. "Hope you're not upset. Didn't want to rush you into this stuff." Melanie rubs his back, smiling. "We've been hoping you'd bring things up yourself, but..." Cole just looks between their bare bodies, his pajama pants tenting quite a bit. He jumps when two hands rub over it, both Melanie and Bee groping him. "I'm...not experienced with stuff like this. Not sure how good I'll be." Bee kisses his cheek, then swaps places with Melanie, now laying at the head of the bed. "Nobody starts out that good. Takes experience."

As he processes this, Melanie strips him of his clothes, all three women staring when his shaft springs free. "Geez Cole, that thing's pretty big. Sure you can handle it Melanie?" The girl has to take a moment, then simply shrugs. "No idea...but I want to be his first." She wiggles between Cole and Bee, then lifts her hips. "I'll walk you through it. She's plenty wet enough, so just hold her hips with one hand, and use the other to guide yourself inside. Go easy, though. She'll need to adjust to that thing you're packing." Following the given instructions, he slowly begins feeding his eight inches into Melanie, while watching her bury her head between Bee's thighs, making him throb inside her.

It takes several minutes, but he does eventually bury fully inside her, a small bulge on her stomach. Starting slow, he thrusts into her, being instructed further by Bee. It was a bit hard for her to give in-depth instructions with Melanie hungrily tending to her pussy. Though his back was to her, he could hear Sonya stroking herself harder, the typically silent woman moaning softly. Thanking his mostly-forgotten nightmare for waking him at just the right time, he picks up speed. Her insides felt so amazing, the way they gripped and squeezed. The heat around his shaft, and the way she pushed back on him when he fully buried inside her.

Given his inexperience, he didn't have the longest fuse...but neither did Melanie. The two end up climaxing together, his seed pumping into the girl. Despite an impressive volley inside her, he was still very hard. She eases off of him, moving aside to rest. She'd been worked on by Bee before Cole was involved. That left a still-hard pre-teen and Bee. Pulling him to her, she then pushes him on his back, straddling him. "My turn. I know you've wanted this for a while. Really need to work on your ogling. Was pretty obvious you've been checking me out." Sinking onto his shaft, she winces. "Fuck...definitely the big man now." She chuckles, then begins bouncing.

While Bee gets her turn on Cole, Melanie looks Sonya over, noticing a somewhat frustrated look on the woman's face. "Feeling left out?" The raven-haired Asian woman nods, seemingly having issues getting herself off. "I've got a little left in the tank." She beckons, then lays back on the bed, her head beside Cole's. He glances over at her just as Sonya pushes into her depths, seeing the look of pleasure on her face. "Oh! Think you and Melanie just got me a cumshot, Sonya." Bee jokes, feeling the hard spurts inside her core. Melanie leans a bit, Cole meeting her half-way for a kiss.

Continuing her ride, Bee eventually milks Cole dry, bouncing and huffing in his lap, his hands groping and squeezing her breasts. Sonya, meanwhile, roughly bites at Melanie's neck, hammering into the pre-teen with a desperate need for release. Usually, she only got to empty in Bee or Allison. It was rare for anyone outside those two to even see her dick, let alone feel it spearing their depths. Eventually, Bee and Cole just sit on the bed, recovering while they watch Sonya absolutely pound into the girl. An arching of the back, and a fifth load pumped into Melanie later, the shaft is finally pulled free, softening.

Bee and Sonya help Cole and Melanie clean up in the bathroom, then tidy the guest room. Looking at one another, they smirk and walk out, leaving the pre-teen couple alone on the bed. "Want to..." "Sure!" Melanie lays back on the bed, Cole pushing into her again. This time, they go easy. Less frantic and heated, more loving and intimate. Exploring one another, exhausting one another with lust and affection, they fall asleep pressed together, Cole's arms wrapped around Melanie's waist. Peeking in on the couple, Bee and Sonya chuckle, heading back down the stairs, where Allison was stirring. "Hey, you two. I miss anything?" Snorting, Bee breaks into laughter, Sonya soon following. "Sure did. Sit down, and we'll catch you up."


	2. Aware

Having slept better than he could remember, Cole wakes to a warmth, looking down to see the blanket bobbing. Lifting it, he sees Melanie sliding her mouth up and down his shaft, only managing about three of his eight inches. Letting out a surprised squeak, he alerts his friend to his awakening, her only response being to wink at him. Not one to look a gift horse in the mouth, he leans back, watching his cute girlfriend work. Something about seeing her do this was incredibly hot, not to mention she was fairly good at it, likely thanks to Sonya. This pleasant little wake-up is ended when he tenses, firing cum into her mouth, which she makes a show of swallowing. The two then dress and head downstairs for breakfast.

At the table, Allison keeps giving both little smirks, which make both pre-teens blush. Now that things were in the open, Bee and Sonya showed blatant affection to both, with little touches and kisses. But, Cole noticed Sonya staring at him several times while they ate. Considering it was a Saturday, none of them really had anything to do, so Bee suggested a mall trip. Cole's parents were quite well off, and made sure he had a nice allowance just for things like this, so he offered to handle buying things. Since they wouldn't all fit in Bee's jeep, they opted for Sonya's SUV, which she'd driven herself and Allison to Cole's place in.

Loading into the vehicle, Allison and Melanie sit on either side of Cole, while Bee sits up front and Sonya drives. It wasn't even ten minutes before his pants are down, and Allison is admiring his dick, whistling softly. "You said it was big, but you didn't mention how nice it looks..." A soft squeak escapes his lips when she starts stroking him, throbbing hard in her grasp. She gives a look to Melanie, who nods and slips out of her seat. The two girls kneel in front of him, kissing and feeling each other up, specifically to get him going more. Once precum begins leaking from his tip, Allison laps it up.

Sitting in the passenger seat, Bee pulls out a little pocket camera, recording the unfolding scene. No sense in using her phone and risking **that** getting around. She wasn't eager to spend a stint in prison. She watches the two girls lick and kiss over the pulsing shaft, biting her lip a bit, trying to ignore her own growing arousal. Cole ws beside himself, still not used to doing sexual things, given his first time had been early that morning. Eventually unable to hold back, he lets loose, splattering Allison and Melanie's faces and tongues with his seed. The two lick one another clean, sharing another kiss before cleaning him up and helping him get his clothes fixed up.

Pulling into the mall's parking lot, the five get out, Cole's walk noticeably a bit lopsided. To his surprise, Sonya steps beside him, helping steady his stride with a smirk. Even someone as clueless as him was starting to get what she was up to. Opting to 'behave' themselves while inside, they have a fairly nice time shopping. Allison and Sonya pick out some clothes for Melanie, and they stop in at the food court to have lunch. Not anything amazing, but it was definitely fun. It was nice to just hang out and let everything else fall out of his mind.

Returning to the house, Allison and Bee take Melanie up to her guest room to help her with her clothes. That left Sonya and Cole alone. And he had this anxious knot in his stomach. She glances over at him, then smiles again. "This morning. What did you think?" The sudden question caught him off guard, making him take a beat longer to figure out her meaning. "You mean your...uh...?" She nods, and he shifts a bit in his seat. "It wasn't...bad, I guess. I've only seen mine, so I can't really judge." She then lays her hand on his thigh, leaning into him some. "You know, Melanie asked me to teach her so she'd be good for you."

Well, that didn't help. As evidenced by the growing bulge in his jeans. She lays her hand directly over it, rubbing slowly. "I wouldn't mind feeling this inside me, like Bee and Melanie did. And I want it before Allison." That knot was getting bigger now. The ride to the mall had made Allison's intent clear, but Sonya was still a mystery. He nearly jumps off the couch when he feels his hand touch something warm and hard. She'd just hiked her skirt, pulled out her shaft and put his hand on it. All while he was lost in thought.

He had no idea what he was doing, or even why, but as his hand stroked along her shaft, the look of pleasure on her face weakened his resolve quite a bit. He could see her building the nerve to ask something, when the sound of a throat being cleared draws his eye. At the entry to the living room stand Bee and Allison, along with Melanie...who was now dressed in what Cole could only describe as 'slutty schoolgirl'. Definitely an Allison choice. "Don't let us interrupt." His girlfriend remarked, smirking playfully at him. The three seat themselves to watch, eyes fixated on his hand pumping along Sonya's cock.

Having an audience like this was weird. He felt his nerve start to falter, his grip loosening. A hand on his back bolsters him a bit, Melanie rubbing up and down his spine. "Don't stop. We want to see." Well, now he had to continue. His grip tightens, hand pumping faster. Eventually, Sonya finds her own nerve. "Cole...will you..." Before she finishes, he gives her a hard kiss, then leans down, tongue touching her tip. A sharp intake of air from both Sonya and Melanie follows, all three spectators taking up positions right in front of the couch, watching with wide eyes.

Deciding to just go for it, he shifts onto all fours on the couch, taking the cockhead between his lips. He remembered what Melanie had done during her pleasant wake-up call, so followed that. Head bobbing up and down, only taking a couple inches, though she was a bit smaller than his, clocking in at around four-five inches, close to half his own length. A hand teases through his hair, her hips bucking gently against him, not wanting to hurt him or force more into his mouth than he was willing to take. Within only ten minutes of starting his suction, he was tasting her cum, shot in thick spurts across his tongue. And to his surprise, it wasn't anywhere near what he expected. It actually tasted pretty good.

Sonya has to take a few minutes, staring at him adoringly while he wipes his mouth. "She takes stuff to make it taste better." Allison chimes in, answering an unspoken question. _Definitely need to take some myself..._ He notes mentally, then sits beside Sonya, needing to recover a bit himself. Everyone sits in silence, then the raven-haired woman speaks again. "Can I take your a-" Before she can finish, Cole puts a finger to her lips. "Not here. If I'm doing that, I'm doing it on a bed so I don't end up face-first on the floor." He absolutely had no faith he could stay on the couch if she went inside.

Laying back on his bed, he bites his lip. This was it, the point of no return. Since Melanie had never done anal, it was on Bee and Allison to help prepare him. Well, Allison had made sure Sonya was all lubed up, while Bee had taken a certain pleasure in fingering his back door, using the opportunity to tease him a bit with her fingers. Sonya lines up, easing into him gently, not wanting to hurt him more than absolutely necessary. It was a strange feeling, having something push inside like that. Part of him had to wonder if that was how women felt their first time.

Sonya takes her time, one hand on his hip, the other keeping her shaft steady. If it had been something his own size, he could never have taken it, but...hers was both shorter and thinner, making for easier penetration. After a couple minutes, she's fully inside him, letting him adjust. Once he gives her a nod, she starts to actually thrust, swaying her hips back and forth with a practices ease. He'd been too pre-occupied when she was plowing Melanie to notice, but she was **very** good at sex in general. It only took a minute or so for him to start moaning, cock throbbing and bouncing as she takes his anal virginity.

Leaning over him, she thrusts faster, picking up speed as he adjusted, eventually just rutting him like she had Melanie. Blue and purple splotches blink across his vision, feeling his shaft rub against her, his lips found by hers. Despite her needy pace, she was a surprisingly gentle kisser. But, his tightness was just too much for her to handle for long, resulting in hard ropes of cum hammering into his depths. His back arches, a loud cry of pleasure escaping his lips as he paints her stomach with his cum. She waits a few moments, then pulls free. Cleaning him up, she lets him lay there and rest, heading back downstairs.

In the living room, she sits on the couch, sighing happily. Having opted not to spectate for his first time, Bee, Melanie and Allison look over, smirking. "Cole's getting better. Think he's getting used to this quicker than we expected. By the time his parents get back tomorrow night, he'll be able to go a couple times." Melanie snorts, leaning on Bee. "He always was quick to pick up new things." She nudges Allison, rubbing her leg. "Once he's ready, I want to watch you two." Allison nods, giving her a firm kiss before moving to settle with Sonya. The four relax, watching night roll in.


	3. Alive

Waking with a start, Cole slowly sits up in bed. He was a little sore from his first time with Sonya, but it could have been worse. Lucky for him, she was gentle. Taking a shower to relax a bit, he walks down the stairs to a very pleasant sight: Bee on all fours, Sonya ramming hard into her folds, head buried between Melanie's legs. Allison was watching intently, a hand under her skirt. Taking in the view for a moment, he decides to make a move of his own for a change, instead of being at their mercy.

Moving up beside Allison, he rests his dick against her cheek, acting as if nothing were out of the ordinary. "Is it me, or do things get wilder at night? Last night, then tonight...almost like our inhibitions go away when the sun does..." Startled by his sudden arrival, the trio on the couch turn to look, Allison already sucking him. His hands tangle in her red hair, motioning his head to Sonya, Bee and Melanie. "Don't let me interrupt. You're not the only ones who like to watch." His confidence had taken a big step up from just two days ago.

With a warm mouth around his throbbing shaft, he enjoys the show, Sonya going even harder, making Bee whimper before her hole is filled with cum, Melanie orgasming against her lips and tongue. Waiting until they finish, he relaxes, flooding Allison's mouth with his seed, remaining very hard after. Stepping away, he swaps with the redhead, sitting in the chair and patting his lap. She strips bare, resting in his lap, reverse cowgirl style. She lifts for just a moment, letting him get in place, then sinks directly onto his rigid length, shuddering as it sinks deep inside. "Oh, fuck...second best cock I've ever sat on." She shivers, blowing Sonya a kiss.

Up and down she bounces, Melanie and Bee watching intently. Sonya was as well, but also rapidly stroked herself, all three watching his rod enter the hot folds in his lap. In this position, they were seated just right to have a great view. Melanie specifically looked ready to burst, biting her lip and starting to grope over herself. Allison was lost in lust and pleasure, making perverse gasps and whines. He'd definitely picked up on things quickly, leaving the sex-loving cheerleader drooling while he bounced her atop himself.

Leaning in, Melanie licks along his shaft, tongue flicking on Allison's clit as well, making both participants groan. "Come on Cole...cum inside her. Do it for me." He'd never heard Melanie talk like that before, but it hit the right spot. He throbs, then erupts inside the hole, feeding her depths multiple shots of hot cum. Bee helps the spent woman onto the couch, Sonya taking the chance to push Melanie's head down on the cock, now covered in his cum and Allison's juices.

While she sucked, Sonya pushed hard and deep into her pussy, holding her hips and savagely fucking the girl. Still trying to recover from his climax inside Allison, the teen boy is completely overwhelmed, grabbing the blonde by the hair, thrusting into her mouth. Caught between two needy, hard cocks, all Melanie can do is rock back and forth, moaning hard as she's used. Whimpering, she orgasms hard, body trembling. Seeing this, Cole unloads inside her mouth, Sonya spilling into her depths.

It takes an hour or so for everyone to fully recover, Cole still being somewhat sensitive. Sonya said it would pass as he had more sex, but he had to admit that didn't help right now, what with Bee licking over the shaft. She slides into his lap, making him especially glad for the large chair now. He'd originally thought it was stupid to have such large furniture. Not anymore. Gasping as she eases herself down onto him, he runs his hands up her stomach, groping her breasts. Their pace was much more gentle than he'd been with Allison, enjoying her warmth and the way she clenched on him.

Rocking up into Bee's depths, he hears a shocked grunt, only one explanation coming to mind: Allison had dug out her toys, and was now giving Sonya a taste of her own medicine with Melanie's help. A brief little glance to the couch confirmed this, the black-haired woman pinned between the other girls, cock visibly leaking. It made him glad his parents wouldn't be home until the next night. Gave them time to make the house not smell like an orgy. That little thought is derailed when Bee kisses him, then whispers in his ear. "Cum for me, Cole." As if on command, he pumps her depths with his seed, grunting and huffing with the effort.

After finishing with Sonya, Melanie comes over and steals Cole's lap, just relaxing against him. They watch Bee, Sonya and Allison go a few rounds, trading up positions as needed. During the show, the two younger teens feel themselves getting hot again, so Melanie turns to face Cole, taking him inside her. "Don't be gentle this time, Cole." She leans down, kissing his lips. "I'm not your girlfriend right now. Just a slut that needs a good fuck." Before she can say anything else, she's holding onto the chair for dear life, her hips slapping hard and loud on his as he thrusts.

Leaning back, she bites her lip and moans, making no attempts to stifle her pleasured voice. Following suit, Cole lets loose too, grunting and moaning as he ravages her depths with rough, harsh thrusts. Caught off guard by the couple's sudden violent sex, Sonya, Allison and Bee watch in stunned silence as the two bring one another to several orgasms before Melanie finally collapses against him, panting and kissing him hard. "Everything I want in a guy...and the only guy I even look at." She smiles, the two sharing a much more loving kiss.

Helped upstairs by Allison and Bee, Cole and Melanie climb into his bed, actually wearing pajamas, and cuddle up to sleep, having exhausted themselves for the night. Heading back downstairs, the three teens sit on the couch, Sonya sniffing the air. "We'll have to behave tomorrow. Can't let his parents come home to a house reeking of sex." Bee nods, then chuckles. "This has been a fun weekend. Gonna be sad to see it end tomorrow evening. He's definitely more confident now, though. Looks like it'll be the three of us again after this, though. Those two are way too into one another to go it solo with any of us again."


End file.
